Mama Tried was first performed by the Grateful Dead in June 1969. The song was played regularly through 1969 and 1970 and a few times in 1971. It was not performed at all in 1972, 1973 and 1975. From 1976 onward the song was performed every year but after 1985 there were never more than 10 outings in a year. In total the Grateful Dead performed the song over 300 times.

The original Merle Haggard recording of Mama Tried topped the country charts in August 1968. Haggard has said that the song is based on his own experiences and the effect of his time in prison on his mother who for a long time had been his family's sole provider;

She had a boy who was more than wild. I don't know what I'd have done with me if I had been the parent. I was a child that needed two parents and there was a period that came up that my mother just couldn't handle. My dad wasn't there and my older brother tried to step in and of course I resented that. It just got all confused and messed up. Mama certainly did try.